Literature DB >> 21580112

9-Hexyl-3-iodo-9H-carbazole.

Wen-Qian Geng1, Guo-Yi Xu, Hong-Ping Zhou.   

Abstract

In the title mol-ecule, C(18)H(20)IN, the tricyclic carbazole system is essentially planar with the two outer rings forming a dihedral angle of 0.43 (8)°. The crystal packing exhibits no short inter-molecular contacts.

Entities:  

Year:  2009        PMID： 21580112      PMCID： PMC2980261          DOI： 10.1107/S1600536809054415

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For the crystal structures of related carbazole derivatives, see: Zhou et al. (2007 ▶, 2008 ▶); Chen et al. (2009 ▶).

Experimental

Crystal data

C18H20IN M = 377.25 Monoclinic, a = 10.7105 (2) Å b = 4.6816 (10) Å c = 33.9661 (18) Å β = 105.106 (8)° V = 1644.3 (4) Å3 Z = 4 Mo Kα radiation μ = 1.94 mm−1 T = 298 K 0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.594, T max = 0.698 13335 measured reflections 2904 independent reflections 2123 reflections with I > 2σ(I) R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.040 wR(F 2) = 0.164 S = 1.14 2904 reflections 182 parameters 13 restraints H-atom parameters constrained Δρmax = 1.03 e Å−3 Δρmin = −0.61 e Å−3 Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809054415/cv2679sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809054415/cv2679Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C18H20INF(000) = 752
Mr = 377.25Dx = 1.524 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybcCell parameters from 4151 reflections
a = 10.7105 (2) Åθ = 2.6–23.7°
b = 4.6816 (10) ŵ = 1.94 mm−1
c = 33.9661 (18) ÅT = 298 K
β = 105.106 (8)°Bar, colourless
V = 1644.3 (4) Å30.30 × 0.20 × 0.20 mm
Z = 4
Bruker SMART CCD area-detector diffractometer2904 independent reflections
Radiation source: fine-focus sealed tube2123 reflections with I > 2σ(I)
graphiteRint = 0.024
phi and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −12→12
Tmin = 0.594, Tmax = 0.698k = −5→5
13335 measured reflectionsl = −40→40
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164H-atom parameters constrained
S = 1.14w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
2904 reflections(Δ/σ)max = 0.002
182 parametersΔρmax = 1.03 e Å−3
13 restraintsΔρmin = −0.61 e Å−3
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
xyzUiso*/Ueq
I1−0.28721 (3)0.22226 (10)0.854577 (12)0.1016 (3)
N10.2490 (4)0.7102 (7)0.85154 (11)0.0642 (10)
C10.0702 (5)0.6986 (10)0.88720 (15)0.0764 (14)
H10.10780.82880.90750.092*
C2−0.0462 (4)0.5812 (12)0.88584 (12)0.0784 (13)
H2−0.08870.63180.90540.094*
C3−0.1033 (4)0.3863 (11)0.85567 (12)0.0691 (11)
C4−0.0449 (4)0.3024 (9)0.82657 (13)0.0642 (11)
H4−0.08390.16990.80680.077*
C50.1625 (4)0.2277 (9)0.76745 (13)0.0642 (12)
H50.09310.10820.75610.077*
C60.2669 (5)0.2482 (9)0.75017 (15)0.0733 (14)
H60.26750.14060.72720.088*
C70.3691 (4)0.4269 (11)0.76693 (14)0.0752 (12)
H70.43730.43940.75480.090*
C80.3731 (4)0.5878 (10)0.80120 (12)0.0677 (11)
H80.44330.70530.81250.081*
C90.1323 (4)0.6213 (9)0.85775 (11)0.0588 (10)
C100.0761 (3)0.4209 (9)0.82713 (10)0.0550 (9)
C110.1639 (3)0.3892 (9)0.80204 (10)0.0543 (9)
C120.2694 (3)0.5687 (8)0.81814 (10)0.0544 (9)
C130.3408 (4)0.9010 (10)0.87894 (12)0.0705 (11)
H13A0.29381.03350.89170.085*
H13B0.38791.01100.86330.085*
C140.4357 (5)0.7305 (8)0.91164 (16)0.0714 (13)
H14A0.38780.62820.92780.086*
H14B0.47770.58990.89850.086*
C150.5381 (4)0.9110 (11)0.93974 (13)0.0745 (12)
H15A0.57771.03280.92330.089*
H15B0.49671.03400.95550.089*
C160.6420 (6)0.7450 (10)0.96843 (19)0.096 (2)
H16A0.67730.60770.95280.115*
H16B0.60370.63860.98680.115*
C170.7505 (5)0.9222 (13)0.99323 (18)0.118 (2)
H17A0.77971.05120.97510.142*
H17B0.71781.03781.01210.142*
C180.8625 (7)0.7562 (13)1.0167 (3)0.144 (3)
H18A0.92360.88261.03400.216*
H18B0.90300.66090.99830.216*
H18C0.83380.61701.03320.216*
U11U22U33U12U13U23
I10.0687 (3)0.1321 (5)0.1158 (4)−0.00227 (17)0.0452 (3)0.0162 (2)
N10.054 (2)0.068 (2)0.065 (2)−0.0032 (16)0.0064 (16)−0.0033 (15)
C10.075 (3)0.086 (3)0.066 (3)0.011 (2)0.015 (2)−0.003 (2)
C20.073 (3)0.104 (4)0.063 (2)0.018 (3)0.027 (2)0.009 (3)
C30.055 (2)0.088 (3)0.068 (2)0.012 (2)0.0223 (19)0.017 (2)
C40.055 (2)0.074 (3)0.061 (2)0.002 (2)0.0105 (18)0.0064 (19)
C50.052 (2)0.073 (3)0.064 (2)−0.0023 (18)0.0103 (19)−0.0076 (18)
C60.066 (3)0.086 (4)0.069 (3)0.001 (2)0.021 (2)−0.009 (2)
C70.058 (2)0.087 (3)0.086 (3)0.003 (2)0.029 (2)0.008 (3)
C80.054 (2)0.069 (3)0.079 (3)−0.006 (2)0.0164 (19)0.002 (2)
C90.055 (2)0.064 (2)0.054 (2)0.009 (2)0.0071 (17)0.0056 (19)
C100.046 (2)0.062 (2)0.0530 (19)0.0080 (19)0.0067 (15)0.0101 (18)
C110.0456 (19)0.060 (2)0.055 (2)0.0056 (18)0.0092 (15)0.0071 (17)
C120.0479 (19)0.057 (2)0.0555 (19)0.0039 (18)0.0089 (15)0.0050 (17)
C130.071 (3)0.062 (3)0.071 (2)−0.005 (2)0.006 (2)−0.006 (2)
C140.071 (3)0.062 (3)0.077 (3)−0.004 (2)0.010 (2)−0.0026 (19)
C150.068 (3)0.079 (3)0.075 (3)−0.015 (2)0.014 (2)−0.009 (2)
C160.099 (5)0.080 (4)0.089 (4)0.006 (3)−0.009 (3)−0.008 (2)
C170.118 (4)0.090 (4)0.121 (4)0.005 (4)−0.014 (3)−0.021 (3)
C180.116 (6)0.135 (6)0.155 (6)0.007 (4)−0.011 (5)−0.028 (4)
I1—C32.106 (4)C9—C101.413 (6)
N1—C121.379 (5)C10—C111.431 (5)
N1—C91.385 (6)C11—C121.400 (5)
N1—C131.467 (5)C13—C141.522 (6)
C1—C21.351 (7)C13—H13A0.9700
C1—C91.386 (7)C13—H13B0.9700
C1—H10.9300C14—C151.511 (6)
C2—C31.389 (7)C14—H14A0.9700
C2—H20.9300C14—H14B0.9700
C3—C41.358 (6)C15—C161.492 (7)
C4—C101.405 (6)C15—H15A0.9700
C4—H40.9300C15—H15B0.9700
C5—C111.394 (6)C16—C171.496 (8)
C5—C61.395 (7)C16—H16A0.9700
C5—H50.9300C16—H16B0.9700
C6—C71.378 (7)C17—C181.477 (7)
C6—H60.9300C17—H17A0.9700
C7—C81.378 (6)C17—H17B0.9700
C7—H70.9300C18—H18A0.9600
C8—C121.381 (5)C18—H18B0.9600
C8—H80.9300C18—H18C0.9600
C12—N1—C9108.9 (3)C8—C12—C11122.1 (4)
C12—N1—C13126.2 (4)N1—C13—C14110.7 (4)
C9—N1—C13124.6 (4)N1—C13—H13A109.5
C2—C1—C9118.8 (5)C14—C13—H13A109.5
C2—C1—H1120.6N1—C13—H13B109.5
C9—C1—H1120.6C14—C13—H13B109.5
C1—C2—C3121.1 (4)H13A—C13—H13B108.1
C1—C2—H2119.4C15—C14—C13113.9 (4)
C3—C2—H2119.4C15—C14—H14A108.8
C4—C3—C2121.9 (4)C13—C14—H14A108.8
C4—C3—I1119.2 (4)C15—C14—H14B108.8
C2—C3—I1118.9 (3)C13—C14—H14B108.8
C3—C4—C10118.3 (4)H14A—C14—H14B107.7
C3—C4—H4120.9C16—C15—C14114.6 (4)
C10—C4—H4120.9C16—C15—H15A108.6
C11—C5—C6118.9 (4)C14—C15—H15A108.6
C11—C5—H5120.6C16—C15—H15B108.6
C6—C5—H5120.6C14—C15—H15B108.6
C7—C6—C5120.4 (4)H15A—C15—H15B107.6
C7—C6—H6119.8C15—C16—C17114.6 (4)
C5—C6—H6119.8C15—C16—H16A108.6
C6—C7—C8121.8 (4)C17—C16—H16A108.6
C6—C7—H7119.1C15—C16—H16B108.6
C8—C7—H7119.1C17—C16—H16B108.6
C7—C8—C12117.7 (4)H16A—C16—H16B107.6
C7—C8—H8121.1C18—C17—C16114.5 (5)
C12—C8—H8121.1C18—C17—H17A108.6
N1—C9—C1130.8 (4)C16—C17—H17A108.6
N1—C9—C10108.4 (4)C18—C17—H17B108.6
C1—C9—C10120.8 (4)C16—C17—H17B108.6
C4—C10—C9119.1 (4)H17A—C17—H17B107.6
C4—C10—C11134.2 (4)C17—C18—H18A109.5
C9—C10—C11106.7 (3)C17—C18—H18B109.5
C5—C11—C12119.0 (4)H18A—C18—H18B109.5
C5—C11—C10133.9 (4)C17—C18—H18C109.5
C12—C11—C10107.1 (3)H18A—C18—H18C109.5
N1—C12—C8128.9 (4)H18B—C18—H18C109.5
N1—C12—C11109.0 (3)
C9—C1—C2—C30.1 (7)C6—C5—C11—C10180.0 (4)
C1—C2—C3—C40.7 (7)C4—C10—C11—C5−0.1 (7)
C1—C2—C3—I1−178.2 (3)C9—C10—C11—C5−179.3 (4)
C2—C3—C4—C10−0.8 (6)C4—C10—C11—C12179.4 (4)
I1—C3—C4—C10178.1 (3)C9—C10—C11—C120.2 (4)
C11—C5—C6—C7−0.5 (7)C9—N1—C12—C8−179.2 (4)
C5—C6—C7—C80.8 (7)C13—N1—C12—C8−5.2 (6)
C6—C7—C8—C12−1.1 (7)C9—N1—C12—C110.9 (4)
C12—N1—C9—C1179.5 (4)C13—N1—C12—C11175.0 (4)
C13—N1—C9—C15.4 (7)C7—C8—C12—N1−178.6 (4)
C12—N1—C9—C10−0.8 (4)C7—C8—C12—C111.2 (6)
C13—N1—C9—C10−175.0 (3)C5—C11—C12—N1178.9 (3)
C2—C1—C9—N1178.8 (4)C10—C11—C12—N1−0.7 (4)
C2—C1—C9—C10−0.8 (6)C5—C11—C12—C8−1.0 (6)
C3—C4—C10—C90.1 (5)C10—C11—C12—C8179.5 (4)
C3—C4—C10—C11−179.1 (4)C12—N1—C13—C14−84.0 (5)
N1—C9—C10—C4−179.0 (3)C9—N1—C13—C1489.2 (5)
C1—C9—C10—C40.7 (6)N1—C13—C14—C15176.8 (4)
N1—C9—C10—C110.4 (4)C13—C14—C15—C16−172.3 (5)
C1—C9—C10—C11−179.9 (4)C14—C15—C16—C17174.0 (6)
C6—C5—C11—C120.6 (6)C15—C16—C17—C18−170.8 (7)
  3 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  9-Butyl-9H-carbazole.

Authors:  Lei Chen; Wei Cheng; Guang-Liang Song; Hong-Jun Zhu
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-02-21

3.  9-Ethyl-3,6-bis-(1H-imidazol-1-yl)-9H-carbazole.

Authors:  Hong Ping Zhou; Liang Fei Lv; Peng Wang; Ren Tao Hu
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-05-14
  3 in total

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